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Retrospective
Tacking with the Wind

Lessons From Being a Creative Director by Hiromi Matsumoto

Rob Trahan

Partner, Mass Productive

Originally published: November 11, 2024

At the close of the 20th century, the internet was experiencing a massive growth spurt. Companies—eager to seize the possibilities of an online presence—jumped on the bandwagon without fully understanding where success would come from. For many young enthusiasts like myself, with no formal training in design or development, this was a golden opportunity to learn by doing.

The Need to Be Self-Made

As an introvert, I was most content spending my free time alone. This probably explains why I excelled at visual art—it was something I could produce without relying on anyone else. When I began showcasing my work online, I realized that building a digital presence could be an art form in itself. Determined to be self-reliant, I dove into books on HTML, earned a Webmaster Certification, and developed websites for local businesses. These efforts eventually landed me my first professional position at Risdall Advertising Agency in Minneapolis.

The truth is, I wasn’t ready. Client meetings were intimidating, and I often found myself nodding along while frantically researching answers afterward. The tools we used were rudimentary compared to today’s standards, but that’s what made the experience exhilarating. We were all experimenting with the possibilities of digital design. It was a time of limitless potential, and we were figuring it out as we went.

Catching My First Break

I was fortunate at this time to work with Stuart Sandler, a brilliant type designer. Though he had nothing to gain, he generously shared his knowledge, showing me how to push the boundaries of our early design tools. His mentorship gave me confidence, and as my skills grew, so did my desire to bring big ideas to life for our clients. I found my creative voice, but this newfound confidence also came with some early misconceptions about what made me valuable.

In the wake of 9/11, the economy took a hit, and like many businesses, our agency had to get creative to stay afloat. John Risdall, the agency owner, introduced company-wide brainstorming sessions to generate new business. When I pitched an interactive campaign concept for an international cosmetics company, it landed—and I felt like I had arrived. That campaign became a major account, and I was convinced my creative brilliance was the key to the agency’s success.

A Need for Self-Reflection

But there was a problem with this thinking. I saw myself as a visionary, believing that the value I brought to the table was in my creativity and the raw merits of my work. As a result, I became rigid. When account executives asked for designs based on ideas I didn’t like, I pushed back. I wasn’t interested in working on things I didn’t believe in. That attitude quickly alienated me from some of my colleagues. When I asked a coworker why I wasn’t being asked to work on certain projects, they told me I had earned a reputation for being difficult to work with. 

This was a turning point. 

During one of my solitary lunches at a nearby lake, I watched sailboats zigzag across the water, catching the wind in different directions. It struck me that their path couldn’t form a straight line—the wind demanded adaptation and compromise for its support. In that moment I realized that I, too, may need to tack back and forth to reach my goals. Collaboration and compromise were essential, and my value wasn’t just in generating brilliant ideas—it was in working as part of a team to bring those ideas to life.

A Rising Tide Lifts All Boats

This realization shifted my entire approach. I began spending more time with coworkers, listening to their challenges and understanding their motivations. Instead of pushing my ideas relentlessly, I learned to embrace the importance of working together to move the project forward. Over time, this mindset allowed me to grow into an effective creative director.

Success isn’t about individual brilliance—it’s about learning to adapt, collaborate, and move forward together

Years later, a client revealed to me that she often found success in collaborating with her direct competitors. “A rising tide lifts all boats,” she said. 

As the world becomes more interconnected and specialized, the ability to collaborate and rely on each other’s expertise is what will drive progress. In the end, success isn’t about individual brilliance—it’s about gliding forward together.